# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_9
_database_code_depnum_ccdc_archive 'CCDC 2298980'
loop_
_audit_author_name
_audit_author_address
'David Cordes'
;University of St Andrews
United Kingdom
;
_audit_update_record             
;
2023-10-03 deposited with the CCDC.	2023-11-21 downloaded from the CCDC.
;
_audit_creation_date             2023-10-03
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H22 F3 N O4'
_chemical_formula_sum            'C19 H22 F3 N O4'
_chemical_formula_weight         385.37
_chemical_absolute_configuration ad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        P212121
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   9.15002(4)
_cell_length_b                   14.07250(7)
_cell_length_c                   14.39225(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1853.199(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    18829
_cell_measurement_temperature    173
_cell_measurement_theta_max      75.3280
_cell_measurement_theta_min      3.0870
_shelx_estimated_absorpt_T_max   0.882
_shelx_estimated_absorpt_T_min   0.841
_exptl_absorpt_coefficient_mu    0.994
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.95742
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.13
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0124
_diffrn_reflns_av_unetI/netI     0.0069
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            21885
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.488
_diffrn_reflns_theta_min         4.394
_diffrn_ambient_temperature      173
_diffrn_detector                 'hybrid photon counting detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Dectris PILATUS P200K'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -125.00  55.00   0.50    2.00    --  -35.00  60.00 -45.00  360
  2  ω   -108.00 -48.00   0.50    2.00    --  -35.00  30.00  90.00  120
  3  ω   -173.50 -10.00   0.50    5.00    -- -100.00  60.00 -90.00  327
  4  ω   -187.00 -40.00   0.50    5.00    -- -100.00  30.00  45.00  294
  5  ω   -165.00 -10.00   0.50    5.00    -- -100.00  60.00-180.00  310
  6  ω   -190.00-127.50   0.50    5.00    -- -100.00  60.00 135.00  125
  7  ω   -165.00 -19.00   0.50    5.00    -- -100.00  60.00   0.00  292
  8  ω   -152.50 -44.50   0.50    5.00    -- -100.00  30.00 135.00  216
  9  ω   -174.00-114.00   0.50    5.00    -- -100.00  60.00  90.00  120
 10  ω    -70.00 -10.00   0.50    5.00    -- -100.00  30.00   0.00  120
 11  ω   -190.00 -10.00   0.50    5.00    -- -100.00  30.00 -90.00  360
 12  ω   -174.00 -10.00   0.50    5.00    -- -100.00  60.00  45.00  328
 13  ω   -190.00-120.00   0.50    5.00    -- -100.00  60.00-135.00  140
;
_diffrn_measurement_device       'AFC11: Quarter χ 4 circle'
_diffrn_measurement_device_type  'Rigaku XtaLAB P200K'
_diffrn_measurement_method       'shutterless scans'
_diffrn_measurement_specimen_support Loop
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0777691000
_diffrn_orient_matrix_UB_12      0.0515914000
_diffrn_orient_matrix_UB_13      0.0804094000
_diffrn_orient_matrix_UB_21      0.1475359000
_diffrn_orient_matrix_UB_22      -0.0123917000
_diffrn_orient_matrix_UB_23      -0.0500394000
_diffrn_orient_matrix_UB_31      -0.0227708000
_diffrn_orient_matrix_UB_32      0.0957964000
_diffrn_orient_matrix_UB_33      -0.0498641000
_diffrn_radiation_monochromator  'Rigaku Osmic Confocal Optical System'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating Anode'
_diffrn_source_type              'Rigaku MM-007HF'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.743
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.984
_reflns_number_gt                3790
_reflns_number_total             3801
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       
'CrystalClear-SM Expert 2.1 b45 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SIR2011  (Burla et al.,  2007)'
_refine_diff_density_max         0.320
_refine_diff_density_min         -0.279
_refine_diff_density_rms         0.059
_refine_ls_abs_structure_details 
;
 Flack x determined using 1605 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.025(18)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.105
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     249
_refine_ls_number_reflns         3801
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0316
_refine_ls_R_factor_gt           0.0315
_refine_ls_restrained_S_all      1.105
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0456P)²+0.3585P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0825
_refine_ls_wR_factor_ref         0.0826
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 N9-H9
 0.98 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 C6(H6)
3.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C7(H7A,H7B), C10(H10A,H10B), C20(H20A,
 H20B)
3.c Aromatic/amide H refined with riding coordinates:
 C12(H12), C13(H13), C14(H14), C15(H15), C16(H16)
3.d Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.14232(19) 0.31895(13) 0.70334(12) 0.0690(5) Uani 1 1 d . . . . .
F2 F 0.3203(2) 0.41231(10) 0.73322(9) 0.0667(5) Uani 1 1 d . . . . .
F3 F 0.35324(17) 0.28921(10) 0.65136(9) 0.0508(4) Uani 1 1 d . . . . .
O2 O 0.40134(16) 0.58825(12) 0.63798(10) 0.0421(3) Uani 1 1 d . . . . .
O8 O 0.31374(14) 0.26179(10) 0.44641(10) 0.0332(3) Uani 1 1 d . . . . .
O18 O 0.22381(17) 0.54406(10) 0.43453(9) 0.0380(3) Uani 1 1 d . . . . .
O19 O 0.09501(15) 0.65282(9) 0.51355(9) 0.0327(3) Uani 1 1 d . . . . .
N9 N 0.11212(17) 0.18628(11) 0.50016(11) 0.0292(3) Uani 1 1 d D . . . .
H9 H 0.020(2) 0.1918(16) 0.5259(15) 0.030(5) Uiso 1 1 d D . . . .
C1 C 0.16734(19) 0.51682(12) 0.59717(11) 0.0247(3) Uani 1 1 d . . . . .
C2 C 0.2750(2) 0.57635(13) 0.65811(12) 0.0295(4) Uani 1 1 d . . . . .
C3 C 0.1937(3) 0.61557(16) 0.74061(14) 0.0419(5) Uani 1 1 d . . . . .
H3A H 0.221188 0.682629 0.751853 0.050 Uiso 1 1 calc R U . . .
H3B H 0.215602 0.578108 0.797138 0.050 Uiso 1 1 calc R U . . .
C4 C 0.0321(3) 0.60789(16) 0.71562(15) 0.0419(5) Uani 1 1 d . . . . .
H4A H -0.001935 0.666701 0.684696 0.050 Uiso 1 1 calc R U . . .
H4B H -0.027561 0.597251 0.772032 0.050 Uiso 1 1 calc R U . . .
C5 C 0.0204(2) 0.52283(14) 0.64955(13) 0.0325(4) Uani 1 1 d . . . . .
H5A H -0.061117 0.532153 0.605248 0.039 Uiso 1 1 calc R U . . .
H5B H 0.002597 0.463657 0.684993 0.039 Uiso 1 1 calc R U . . .
C6 C 0.22762(18) 0.41540(12) 0.57853(11) 0.0247(3) Uani 1 1 d . . . . .
H6 H 0.321995 0.422962 0.544282 0.030 Uiso 1 1 calc R U . . .
C7 C 0.12549(19) 0.35705(12) 0.51607(13) 0.0291(4) Uani 1 1 d . . . . .
H7A H 0.033951 0.343625 0.550306 0.035 Uiso 1 1 calc R U . . .
H7B H 0.100000 0.395197 0.460594 0.035 Uiso 1 1 calc R U . . .
C8 C 0.19287(18) 0.26365(12) 0.48479(12) 0.0260(3) Uani 1 1 d . . . . .
C10 C 0.1590(2) 0.09081(13) 0.47388(13) 0.0312(4) Uani 1 1 d . . . . .
H10A H 0.247219 0.095549 0.434370 0.037 Uiso 1 1 calc R U . . .
H10B H 0.080954 0.060425 0.436598 0.037 Uiso 1 1 calc R U . . .
C11 C 0.19272(19) 0.02874(12) 0.55698(13) 0.0282(4) Uani 1 1 d . . . . .
C12 C 0.3030(2) 0.05312(15) 0.61873(15) 0.0365(4) Uani 1 1 d . . . . .
H12 H 0.356103 0.110377 0.609597 0.044 Uiso 1 1 calc R U . . .
C13 C 0.3368(3) -0.00491(17) 0.69355(16) 0.0458(5) Uani 1 1 d . . . . .
H13 H 0.412197 0.012737 0.735553 0.055 Uiso 1 1 calc R U . . .
C14 C 0.2602(3) -0.08881(17) 0.70681(16) 0.0473(5) Uani 1 1 d . . . . .
H14 H 0.284073 -0.129425 0.757301 0.057 Uiso 1 1 calc R U . . .
C15 C 0.1495(3) -0.11312(16) 0.64669(16) 0.0473(5) Uani 1 1 d . . . . .
H15 H 0.096341 -0.170290 0.656202 0.057 Uiso 1 1 calc R U . . .
C16 C 0.1149(2) -0.05460(14) 0.57217(15) 0.0383(4) Uani 1 1 d . . . . .
H16 H 0.037622 -0.071650 0.531360 0.046 Uiso 1 1 calc R U . . .
C17 C 0.2610(2) 0.36026(14) 0.66731(13) 0.0327(4) Uani 1 1 d . . . . .
C18 C 0.16531(19) 0.57039(12) 0.50433(12) 0.0259(3) Uani 1 1 d . . . . .
C20 C 0.0855(2) 0.71220(14) 0.43004(14) 0.0361(4) Uani 1 1 d . . . . .
H20A H 0.005787 0.759056 0.437885 0.043 Uiso 1 1 calc R U . . .
H20B H 0.061293 0.671704 0.375952 0.043 Uiso 1 1 calc R U . . .
C21 C 0.2259(3) 0.76373(16) 0.41139(16) 0.0434(5) Uani 1 1 d . . . . .
H21A H 0.257056 0.797149 0.467745 0.065 Uiso 1 1 calc R U . . .
H21B H 0.211042 0.809774 0.361181 0.065 Uiso 1 1 calc R U . . .
H21C H 0.301267 0.717967 0.393048 0.065 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C17 1.337(3) . ?
F2 C17 1.315(2) . ?
F3 C17 1.328(2) . ?
O2 C2 1.203(2) . ?
O8 C8 1.236(2) . ?
O18 C18 1.197(2) . ?
O19 C18 1.333(2) . ?
O19 C20 1.466(2) . ?
N9 H9 0.927(18) . ?
N9 C8 1.334(2) . ?
N9 C10 1.460(2) . ?
C1 C2 1.563(2) . ?
C1 C5 1.544(2) . ?
C1 C6 1.553(2) . ?
C1 C18 1.534(2) . ?
C2 C3 1.506(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.525(4) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.533(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 H6 1.0000 . ?
C6 C7 1.535(2) . ?
C6 C17 1.526(2) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.520(2) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.513(3) . ?
C11 C12 1.388(3) . ?
C11 C16 1.389(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.386(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.387(4) . ?
C14 H14 0.9500 . ?
C14 C15 1.375(4) . ?
C15 H15 0.9500 . ?
C15 C16 1.389(3) . ?
C16 H16 0.9500 . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C20 C21 1.499(3) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C18 O19 C20 116.29(14) . . ?
C8 N9 H9 120.2(14) . . ?
C8 N9 C10 123.05(15) . . ?
C10 N9 H9 116.6(14) . . ?
C5 C1 C2 104.21(14) . . ?
C5 C1 C6 116.35(14) . . ?
C6 C1 C2 111.45(14) . . ?
C18 C1 C2 103.48(13) . . ?
C18 C1 C5 112.82(14) . . ?
C18 C1 C6 107.78(13) . . ?
O2 C2 C1 123.03(17) . . ?
O2 C2 C3 127.84(19) . . ?
C3 C2 C1 109.12(16) . . ?
C2 C3 H3A 110.6 . . ?
C2 C3 H3B 110.6 . . ?
C2 C3 C4 105.48(16) . . ?
H3A C3 H3B 108.8 . . ?
C4 C3 H3A 110.6 . . ?
C4 C3 H3B 110.6 . . ?
C3 C4 H4A 110.6 . . ?
C3 C4 H4B 110.6 . . ?
C3 C4 C5 105.64(17) . . ?
H4A C4 H4B 108.7 . . ?
C5 C4 H4A 110.6 . . ?
C5 C4 H4B 110.6 . . ?
C1 C5 H5A 110.4 . . ?
C1 C5 H5B 110.4 . . ?
C4 C5 C1 106.54(16) . . ?
C4 C5 H5A 110.4 . . ?
C4 C5 H5B 110.4 . . ?
H5A C5 H5B 108.6 . . ?
C1 C6 H6 107.1 . . ?
C7 C6 C1 112.12(13) . . ?
C7 C6 H6 107.1 . . ?
C17 C6 C1 113.19(14) . . ?
C17 C6 H6 107.1 . . ?
C17 C6 C7 109.90(14) . . ?
C6 C7 H7A 109.0 . . ?
C6 C7 H7B 109.0 . . ?
H7A C7 H7B 107.8 . . ?
C8 C7 C6 112.91(14) . . ?
C8 C7 H7A 109.0 . . ?
C8 C7 H7B 109.0 . . ?
O8 C8 N9 123.51(16) . . ?
O8 C8 C7 120.89(16) . . ?
N9 C8 C7 115.59(15) . . ?
N9 C10 H10A 109.0 . . ?
N9 C10 H10B 109.0 . . ?
N9 C10 C11 112.73(15) . . ?
H10A C10 H10B 107.8 . . ?
C11 C10 H10A 109.0 . . ?
C11 C10 H10B 109.0 . . ?
C12 C11 C10 120.80(17) . . ?
C12 C11 C16 118.72(19) . . ?
C16 C11 C10 120.47(17) . . ?
C11 C12 H12 119.5 . . ?
C13 C12 C11 120.9(2) . . ?
C13 C12 H12 119.5 . . ?
C12 C13 H13 120.1 . . ?
C12 C13 C14 119.7(2) . . ?
C14 C13 H13 120.1 . . ?
C13 C14 H14 120.1 . . ?
C15 C14 C13 119.9(2) . . ?
C15 C14 H14 120.1 . . ?
C14 C15 H15 119.8 . . ?
C14 C15 C16 120.4(2) . . ?
C16 C15 H15 119.8 . . ?
C11 C16 H16 119.8 . . ?
C15 C16 C11 120.3(2) . . ?
C15 C16 H16 119.8 . . ?
F1 C17 C6 112.54(17) . . ?
F2 C17 F1 107.30(18) . . ?
F2 C17 F3 106.37(17) . . ?
F2 C17 C6 113.78(15) . . ?
F3 C17 F1 104.83(17) . . ?
F3 C17 C6 111.42(15) . . ?
O18 C18 O19 124.65(16) . . ?
O18 C18 C1 124.98(15) . . ?
O19 C18 C1 110.29(14) . . ?
O19 C20 H20A 109.2 . . ?
O19 C20 H20B 109.2 . . ?
O19 C20 C21 111.84(17) . . ?
H20A C20 H20B 107.9 . . ?
C21 C20 H20A 109.2 . . ?
C21 C20 H20B 109.2 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N9 H9 O8 0.927(18) 2.033(19) 2.929(2) 162(2) 3_456 yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 C2 C3 C4 161.1(2) . . . . ?
N9 C10 C11 C12 -61.5(2) . . . . ?
N9 C10 C11 C16 119.35(19) . . . . ?
C1 C2 C3 C4 -17.4(2) . . . . ?
C1 C6 C7 C8 171.10(14) . . . . ?
C1 C6 C17 F1 82.8(2) . . . . ?
C1 C6 C17 F2 -39.6(2) . . . . ?
C1 C6 C17 F3 -159.81(16) . . . . ?
C2 C1 C5 C4 18.52(19) . . . . ?
C2 C1 C6 C7 -178.13(14) . . . . ?
C2 C1 C6 C17 56.86(19) . . . . ?
C2 C1 C18 O18 106.1(2) . . . . ?
C2 C1 C18 O19 -70.87(17) . . . . ?
C2 C3 C4 C5 28.9(2) . . . . ?
C3 C4 C5 C1 -29.7(2) . . . . ?
C5 C1 C2 O2 -179.32(18) . . . . ?
C5 C1 C2 C3 -0.68(19) . . . . ?
C5 C1 C6 C7 62.60(19) . . . . ?
C5 C1 C6 C17 -62.4(2) . . . . ?
C5 C1 C18 O18 -141.85(19) . . . . ?
C5 C1 C18 O19 41.1(2) . . . . ?
C6 C1 C2 O2 54.4(2) . . . . ?
C6 C1 C2 C3 -126.94(16) . . . . ?
C6 C1 C5 C4 141.64(16) . . . . ?
C6 C1 C18 O18 -12.0(2) . . . . ?
C6 C1 C18 O19 170.99(14) . . . . ?
C6 C7 C8 O8 -53.4(2) . . . . ?
C6 C7 C8 N9 127.74(16) . . . . ?
C7 C6 C17 F1 -43.4(2) . . . . ?
C7 C6 C17 F2 -165.76(17) . . . . ?
C7 C6 C17 F3 74.0(2) . . . . ?
C8 N9 C10 C11 111.11(19) . . . . ?
C10 N9 C8 O8 0.6(3) . . . . ?
C10 N9 C8 C7 179.41(16) . . . . ?
C10 C11 C12 C13 -178.26(18) . . . . ?
C10 C11 C16 C15 177.77(19) . . . . ?
C11 C12 C13 C14 0.4(3) . . . . ?
C12 C11 C16 C15 -1.4(3) . . . . ?
C12 C13 C14 C15 -1.1(3) . . . . ?
C13 C14 C15 C16 0.7(4) . . . . ?
C14 C15 C16 C11 0.6(3) . . . . ?
C16 C11 C12 C13 0.9(3) . . . . ?
C17 C6 C7 C8 -62.09(19) . . . . ?
C18 O19 C20 C21 -77.9(2) . . . . ?
C18 C1 C2 O2 -61.1(2) . . . . ?
C18 C1 C2 C3 117.49(16) . . . . ?
C18 C1 C5 C4 -93.04(18) . . . . ?
C18 C1 C6 C7 -65.23(17) . . . . ?
C18 C1 C6 C17 169.76(15) . . . . ?
C20 O19 C18 O18 2.5(3) . . . . ?
C20 O19 C18 C1 179.53(15) . . . . ?

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: chloroform'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_20
_database_code_depnum_ccdc_archive 'CCDC 2298982'
loop_
_audit_author_name
_audit_author_address
'David Cordes'
;University of St Andrews
United Kingdom
;
_audit_update_record             
;
2023-10-03 deposited with the CCDC.	2023-11-21 downloaded from the CCDC.
;
_audit_creation_date             2023-10-02
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H21 Cl F2 N2 O5'
_chemical_formula_sum            'C23 H21 Cl F2 N2 O5'
_chemical_formula_weight         478.87
_chemical_absolute_configuration ad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        P212121
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   9.32874(6)
_cell_length_b                   14.99320(9)
_cell_length_c                   16.18409(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2263.63(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    23699
_cell_measurement_temperature    125
_cell_measurement_theta_max      75.2730
_cell_measurement_theta_min      4.0110
_shelx_estimated_absorpt_T_max   0.908
_shelx_estimated_absorpt_T_min   0.827
_exptl_absorpt_coefficient_mu    1.976
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86671
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.405
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             992
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0230
_diffrn_reflns_av_unetI/netI     0.0127
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            26847
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.471
_diffrn_reflns_theta_min         4.019
_diffrn_ambient_temperature      125
_diffrn_detector                 'hybrid photon counting detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Dectris PILATUS P200K'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -125.00  55.00   0.50   10.00    --  -35.00  60.00 -45.00  360
  2  ω   -108.00 -48.00   0.50   10.00    --  -35.00  30.00  90.00  120
  3  ω   -173.50 -10.00   0.50   20.00    -- -100.00  60.00 -90.00  327
  4  ω   -187.00 -40.00   0.50   20.00    -- -100.00  30.00  45.00  294
  5  ω   -165.00 -10.00   0.50   20.00    -- -100.00  60.00-180.00  310
  6  ω   -190.00-127.50   0.50   20.00    -- -100.00  60.00 135.00  125
  7  ω   -165.00 -19.00   0.50   20.00    -- -100.00  60.00   0.00  292
  8  ω   -152.50 -44.50   0.50   20.00    -- -100.00  30.00 135.00  216
  9  ω   -174.00-114.00   0.50   20.00    -- -100.00  60.00  90.00  120
 10  ω    -70.00 -10.00   0.50   20.00    -- -100.00  30.00   0.00  120
 11  ω   -190.00 -10.00   0.50   20.00    -- -100.00  30.00 -90.00  360
 12  ω   -174.00 -10.00   0.50   20.00    -- -100.00  60.00  45.00  328
 13  ω   -190.00-120.00   0.50   20.00    -- -100.00  60.00-135.00  140
;
_diffrn_measurement_device       'AFC11: Quarter χ 4 circle'
_diffrn_measurement_device_type  'Rigaku XtaLAB P200K'
_diffrn_measurement_method       'shutterless scans'
_diffrn_measurement_specimen_support Loop
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0220372000
_diffrn_orient_matrix_UB_12      0.0810441000
_diffrn_orient_matrix_UB_13      0.0570913000
_diffrn_orient_matrix_UB_21      0.0033438000
_diffrn_orient_matrix_UB_22      0.0624137000
_diffrn_orient_matrix_UB_23      -0.0755927000
_diffrn_orient_matrix_UB_31      -0.1636532000
_diffrn_orient_matrix_UB_32      -0.0096910000
_diffrn_orient_matrix_UB_33      -0.0092255000
_diffrn_radiation_monochromator  'Rigaku Osmic Confocal Optical System'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating Anode'
_diffrn_source_type              'Rigaku MM-007HF'
_reflns_Friedel_coverage         0.754
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.983
_reflns_number_gt                4562
_reflns_number_total             4647
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_collection       
'CrystalClear-SM Expert 2.1 b45 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.150
_refine_diff_density_min         -0.333
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details 
;
 Flack x determined using 1936 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.000(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     304
_refine_ls_number_reflns         4647
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0257
_refine_ls_R_factor_gt           0.0254
_refine_ls_restrained_S_all      1.047
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0395P)²+0.4158P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0676
_refine_ls_wR_factor_ref         0.0678
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 N15-H15
 0.98 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 C12(H12)
3.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C16(H16A,H16B)
3.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C8(H8), C18(H18), C19(H19), C20(H20), C21(H21),
 C22(H22)
3.d Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C26(H26A,H26B,H26C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.31703(6) 0.57152(3) 0.45026(3) 0.03955(12) Uani 1 1 d . . . . .
F1 F 0.17849(15) 0.48398(8) 0.55713(8) 0.0469(3) Uani 1 1 d . . . . .
F2 F 0.40906(16) 0.46973(8) 0.56204(8) 0.0457(3) Uani 1 1 d . . . . .
O3 O 0.02250(13) 0.57450(8) 0.71880(8) 0.0288(3) Uani 1 1 d . . . . .
O10 O 0.56534(13) 0.58014(8) 0.73088(8) 0.0300(3) Uani 1 1 d . . . . .
O14 O 0.40607(12) 0.76803(8) 0.55114(8) 0.0291(3) Uani 1 1 d . . . . .
O24 O 0.31259(16) 0.71936(8) 0.75596(8) 0.0360(3) Uani 1 1 d . . . . .
O25 O 0.31938(17) 0.60551(8) 0.84548(8) 0.0365(3) Uani 1 1 d . . . . .
N1 N 0.37538(15) 0.48944(9) 0.72543(9) 0.0230(3) Uani 1 1 d . . . . .
N15 N 0.19167(16) 0.79703(10) 0.49223(9) 0.0282(3) Uani 1 1 d D . . . .
H15 H 0.097(2) 0.7788(17) 0.4864(16) 0.047(7) Uiso 1 1 d D . . . .
C2 C 0.28428(17) 0.56688(10) 0.70632(10) 0.0219(3) Uani 1 1 d . . . . .
C3 C 0.13066(17) 0.52940(11) 0.72027(10) 0.0225(3) Uani 1 1 d . . . . .
C4 C 0.14602(17) 0.43382(11) 0.73411(10) 0.0230(3) Uani 1 1 d . . . . .
C5 C 0.03893(18) 0.36945(11) 0.74075(11) 0.0268(3) Uani 1 1 d . . . . .
H5 H -0.059461 0.385776 0.740280 0.032 Uiso 1 1 calc R U . . .
C6 C 0.0797(2) 0.28129(11) 0.74802(12) 0.0304(4) Uani 1 1 d . . . . .
H6 H 0.009013 0.235887 0.751946 0.037 Uiso 1 1 calc R U . . .
C7 C 0.2249(2) 0.25896(11) 0.74959(12) 0.0301(4) Uani 1 1 d . . . . .
H7 H 0.250938 0.197947 0.754579 0.036 Uiso 1 1 calc R U . . .
C8 C 0.33276(19) 0.32262(10) 0.74412(11) 0.0277(3) Uani 1 1 d . . . . .
H8 H 0.431050 0.306143 0.745766 0.033 Uiso 1 1 calc R U . . .
C9 C 0.29127(17) 0.41172(10) 0.73613(10) 0.0223(3) Uani 1 1 d . . . . .
C10 C 0.51968(18) 0.50409(11) 0.73865(11) 0.0259(3) Uani 1 1 d . . . . .
C11 C 0.61446(19) 0.42786(13) 0.76215(15) 0.0375(4) Uani 1 1 d . . . . .
H11A H 0.617202 0.384445 0.716908 0.056 Uiso 1 1 calc R U . . .
H11B H 0.576791 0.399164 0.812036 0.056 Uiso 1 1 calc R U . . .
H11C H 0.711534 0.449967 0.772915 0.056 Uiso 1 1 calc R U . . .
C12 C 0.30781(18) 0.60373(10) 0.61707(10) 0.0234(3) Uani 1 1 d . . . . .
H12 H 0.406250 0.630088 0.615530 0.028 Uiso 1 1 calc R U . . .
C13 C 0.20273(18) 0.67823(11) 0.59256(11) 0.0259(3) Uani 1 1 d . . . . .
H13A H 0.123808 0.652508 0.559332 0.031 Uiso 1 1 calc R U . . .
H13B H 0.160521 0.704647 0.643073 0.031 Uiso 1 1 calc R U . . .
C14 C 0.27720(17) 0.75103(11) 0.54282(11) 0.0245(3) Uani 1 1 d . . . . .
C16 C 0.2466(2) 0.86772(12) 0.43979(11) 0.0298(4) Uani 1 1 d . . . . .
H16A H 0.186346 0.871093 0.389548 0.036 Uiso 1 1 calc R U . . .
H16B H 0.344829 0.851508 0.422091 0.036 Uiso 1 1 calc R U . . .
C17 C 0.2515(2) 0.95918(13) 0.47918(12) 0.0307(4) Uani 1 1 d . . . . .
C18 C 0.3183(3) 1.02768(14) 0.43621(15) 0.0455(5) Uani 1 1 d . . . . .
H18 H 0.362187 1.015386 0.384470 0.055 Uiso 1 1 calc R U . . .
C19 C 0.3222(3) 1.11305(16) 0.46729(18) 0.0598(7) Uani 1 1 d . . . . .
H19 H 0.370202 1.158797 0.437570 0.072 Uiso 1 1 calc R U . . .
C20 C 0.2560(3) 1.13252(16) 0.54199(17) 0.0544(6) Uani 1 1 d . . . . .
H20 H 0.256193 1.191778 0.562769 0.065 Uiso 1 1 calc R U . . .
C21 C 0.1902(3) 1.06540(16) 0.58561(14) 0.0489(5) Uani 1 1 d . . . . .
H21 H 0.145979 1.078013 0.637168 0.059 Uiso 1 1 calc R U . . .
C22 C 0.1884(2) 0.97898(14) 0.55434(13) 0.0384(4) Uani 1 1 d . . . . .
H22 H 0.143225 0.932885 0.585054 0.046 Uiso 1 1 calc R U . . .
C23 C 0.3039(2) 0.53007(12) 0.55255(12) 0.0321(4) Uani 1 1 d . . . . .
C24 C 0.30952(19) 0.64113(10) 0.77057(11) 0.0262(3) Uani 1 1 d . . . . .
C26 C 0.3420(4) 0.66797(16) 0.91205(14) 0.0588(7) Uani 1 1 d . . . . .
H26A H 0.422400 0.707324 0.898326 0.088 Uiso 1 1 calc R U . . .
H26B H 0.363735 0.635265 0.962963 0.088 Uiso 1 1 calc R U . . .
H26C H 0.255157 0.703727 0.920088 0.088 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C23 1.7725(19) . ?
F1 C23 1.361(2) . ?
F2 C23 1.343(2) . ?
O3 C3 1.215(2) . ?
O10 C10 1.224(2) . ?
O14 C14 1.236(2) . ?
O24 C24 1.197(2) . ?
O25 C24 1.328(2) . ?
O25 C26 1.443(2) . ?
N1 C2 1.472(2) . ?
N1 C9 1.415(2) . ?
N1 C10 1.381(2) . ?
N15 H15 0.93(2) . ?
N15 C14 1.335(2) . ?
N15 C16 1.451(2) . ?
C2 C3 1.556(2) . ?
C2 C12 1.562(2) . ?
C2 C24 1.541(2) . ?
C3 C4 1.457(2) . ?
C4 C5 1.393(2) . ?
C4 C9 1.395(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.380(2) . ?
C6 H6 0.9500 . ?
C6 C7 1.395(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.390(2) . ?
C8 H8 0.9500 . ?
C8 C9 1.397(2) . ?
C10 C11 1.494(2) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12 1.0000 . ?
C12 C13 1.538(2) . ?
C12 C23 1.520(2) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.524(2) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C17 1.513(3) . ?
C17 C18 1.388(3) . ?
C17 C22 1.383(3) . ?
C18 H18 0.9500 . ?
C18 C19 1.376(3) . ?
C19 H19 0.9500 . ?
C19 C20 1.388(4) . ?
C20 H20 0.9500 . ?
C20 C21 1.374(4) . ?
C21 H21 0.9500 . ?
C21 C22 1.391(3) . ?
C22 H22 0.9500 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C24 O25 C26 115.52(15) . . ?
C9 N1 C2 110.80(13) . . ?
C10 N1 C2 118.04(13) . . ?
C10 N1 C9 130.73(14) . . ?
C14 N15 H15 118.6(16) . . ?
C14 N15 C16 121.64(15) . . ?
C16 N15 H15 119.4(16) . . ?
N1 C2 C3 102.49(12) . . ?
N1 C2 C12 113.10(13) . . ?
N1 C2 C24 109.86(13) . . ?
C3 C2 C12 113.05(13) . . ?
C24 C2 C3 107.68(13) . . ?
C24 C2 C12 110.30(13) . . ?
O3 C3 C2 124.13(14) . . ?
O3 C3 C4 129.19(15) . . ?
C4 C3 C2 106.68(13) . . ?
C5 C4 C3 128.50(15) . . ?
C5 C4 C9 122.00(15) . . ?
C9 C4 C3 109.43(14) . . ?
C4 C5 H5 120.9 . . ?
C6 C5 C4 118.18(16) . . ?
C6 C5 H5 120.9 . . ?
C5 C6 H6 120.0 . . ?
C5 C6 C7 119.92(16) . . ?
C7 C6 H6 120.0 . . ?
C6 C7 H7 118.8 . . ?
C8 C7 C6 122.47(16) . . ?
C8 C7 H7 118.8 . . ?
C7 C8 H8 121.2 . . ?
C7 C8 C9 117.52(16) . . ?
C9 C8 H8 121.2 . . ?
C4 C9 N1 109.87(13) . . ?
C4 C9 C8 119.89(15) . . ?
C8 C9 N1 130.17(15) . . ?
O10 C10 N1 118.14(15) . . ?
O10 C10 C11 122.20(16) . . ?
N1 C10 C11 119.65(15) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C2 C12 H12 107.0 . . ?
C13 C12 C2 113.94(13) . . ?
C13 C12 H12 107.0 . . ?
C23 C12 C2 112.01(13) . . ?
C23 C12 H12 107.0 . . ?
C23 C12 C13 109.59(14) . . ?
C12 C13 H13A 109.3 . . ?
C12 C13 H13B 109.3 . . ?
H13A C13 H13B 108.0 . . ?
C14 C13 C12 111.46(13) . . ?
C14 C13 H13A 109.3 . . ?
C14 C13 H13B 109.3 . . ?
O14 C14 N15 122.79(16) . . ?
O14 C14 C13 122.23(15) . . ?
N15 C14 C13 114.93(14) . . ?
N15 C16 H16A 108.5 . . ?
N15 C16 H16B 108.5 . . ?
N15 C16 C17 115.22(15) . . ?
H16A C16 H16B 107.5 . . ?
C17 C16 H16A 108.5 . . ?
C17 C16 H16B 108.5 . . ?
C18 C17 C16 118.22(18) . . ?
C22 C17 C16 123.52(17) . . ?
C22 C17 C18 118.2(2) . . ?
C17 C18 H18 119.4 . . ?
C19 C18 C17 121.1(2) . . ?
C19 C18 H18 119.4 . . ?
C18 C19 H19 119.9 . . ?
C18 C19 C20 120.2(2) . . ?
C20 C19 H19 119.9 . . ?
C19 C20 H20 120.3 . . ?
C21 C20 C19 119.5(2) . . ?
C21 C20 H20 120.3 . . ?
C20 C21 H21 120.0 . . ?
C20 C21 C22 120.1(2) . . ?
C22 C21 H21 120.0 . . ?
C17 C22 C21 121.0(2) . . ?
C17 C22 H22 119.5 . . ?
C21 C22 H22 119.5 . . ?
F1 C23 Cl1 106.75(13) . . ?
F1 C23 C12 110.61(15) . . ?
F2 C23 Cl1 107.02(13) . . ?
F2 C23 F1 106.24(15) . . ?
F2 C23 C12 113.16(16) . . ?
C12 C23 Cl1 112.65(12) . . ?
O24 C24 O25 124.95(16) . . ?
O24 C24 C2 125.31(16) . . ?
O25 C24 C2 109.64(13) . . ?
O25 C26 H26A 109.5 . . ?
O25 C26 H26B 109.5 . . ?
O25 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N15 H15 O14 0.93(2) 2.01(2) 2.923(2) 167(2) 4_466 yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O3 C3 C4 C5 7.2(3) . . . . ?
O3 C3 C4 C9 -175.90(17) . . . . ?
N1 C2 C3 O3 172.60(16) . . . . ?
N1 C2 C3 C4 -7.69(16) . . . . ?
N1 C2 C12 C13 173.88(13) . . . . ?
N1 C2 C12 C23 48.77(18) . . . . ?
N1 C2 C24 O24 141.97(19) . . . . ?
N1 C2 C24 O25 -41.51(19) . . . . ?
N15 C16 C17 C18 172.52(18) . . . . ?
N15 C16 C17 C22 -9.9(3) . . . . ?
C2 N1 C9 C4 -6.37(19) . . . . ?
C2 N1 C9 C8 170.69(17) . . . . ?
C2 N1 C10 O10 -2.6(2) . . . . ?
C2 N1 C10 C11 177.10(16) . . . . ?
C2 C3 C4 C5 -172.49(17) . . . . ?
C2 C3 C4 C9 4.42(18) . . . . ?
C2 C12 C13 C14 140.63(14) . . . . ?
C2 C12 C23 Cl1 175.58(12) . . . . ?
C2 C12 C23 F1 56.20(19) . . . . ?
C2 C12 C23 F2 -62.86(19) . . . . ?
C3 C2 C12 C13 57.97(18) . . . . ?
C3 C2 C12 C23 -67.14(17) . . . . ?
C3 C2 C24 O24 -107.1(2) . . . . ?
C3 C2 C24 O25 69.38(17) . . . . ?
C3 C4 C5 C6 175.40(17) . . . . ?
C3 C4 C9 N1 0.9(2) . . . . ?
C3 C4 C9 C8 -176.46(15) . . . . ?
C4 C5 C6 C7 0.8(3) . . . . ?
C5 C4 C9 N1 178.09(15) . . . . ?
C5 C4 C9 C8 0.7(3) . . . . ?
C5 C6 C7 C8 0.0(3) . . . . ?
C6 C7 C8 C9 -0.5(3) . . . . ?
C7 C8 C9 N1 -176.64(17) . . . . ?
C7 C8 C9 C4 0.2(3) . . . . ?
C9 N1 C2 C3 8.53(17) . . . . ?
C9 N1 C2 C12 -113.50(15) . . . . ?
C9 N1 C2 C24 122.78(14) . . . . ?
C9 N1 C10 O10 -174.28(17) . . . . ?
C9 N1 C10 C11 5.4(3) . . . . ?
C9 C4 C5 C6 -1.2(3) . . . . ?
C10 N1 C2 C3 -164.75(15) . . . . ?
C10 N1 C2 C12 73.22(18) . . . . ?
C10 N1 C2 C24 -50.50(19) . . . . ?
C10 N1 C9 C4 165.80(17) . . . . ?
C10 N1 C9 C8 -17.1(3) . . . . ?
C12 C2 C3 O3 -65.3(2) . . . . ?
C12 C2 C3 C4 114.37(14) . . . . ?
C12 C2 C24 O24 16.6(2) . . . . ?
C12 C2 C24 O25 -166.85(14) . . . . ?
C12 C13 C14 O14 -28.3(2) . . . . ?
C12 C13 C14 N15 154.21(15) . . . . ?
C13 C12 C23 Cl1 48.10(17) . . . . ?
C13 C12 C23 F1 -71.27(18) . . . . ?
C13 C12 C23 F2 169.67(14) . . . . ?
C14 N15 C16 C17 -87.6(2) . . . . ?
C16 N15 C14 O14 3.4(3) . . . . ?
C16 N15 C14 C13 -179.11(15) . . . . ?
C16 C17 C18 C19 177.8(2) . . . . ?
C16 C17 C22 C21 -176.8(2) . . . . ?
C17 C18 C19 C20 -1.4(4) . . . . ?
C18 C17 C22 C21 0.8(3) . . . . ?
C18 C19 C20 C21 1.8(5) . . . . ?
C19 C20 C21 C22 -0.9(4) . . . . ?
C20 C21 C22 C17 -0.4(4) . . . . ?
C22 C17 C18 C19 0.0(4) . . . . ?
C23 C12 C13 C14 -92.99(17) . . . . ?
C24 C2 C3 O3 56.8(2) . . . . ?
C24 C2 C3 C4 -123.53(14) . . . . ?
C24 C2 C12 C13 -62.65(18) . . . . ?
C24 C2 C12 C23 172.25(14) . . . . ?
C26 O25 C24 O24 -3.0(3) . . . . ?
C26 O25 C24 C2 -179.50(19) . . . . ?


#===END
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: chloroform'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_16
_database_code_depnum_ccdc_archive 'CCDC 2298981'
loop_
_audit_author_name
_audit_author_address
'David Cordes'
;University of St Andrews
United Kingdom
;
_audit_update_record             
;
2023-10-03 deposited with the CCDC.	2023-11-21 downloaded from the CCDC.
;
_audit_creation_date             2023-10-03
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H22 F3 N O4'
_chemical_formula_sum            'C23 H22 F3 N O4'
_chemical_formula_weight         433.41
_chemical_absolute_configuration ad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        P212121
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   9.9425(2)
_cell_length_b                   18.8834(3)
_cell_length_c                   22.2420(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4175.90(13)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    29952
_cell_measurement_temperature    173
_cell_measurement_theta_max      66.3980
_cell_measurement_theta_min      3.0570
_shelx_estimated_absorpt_T_max   0.919
_shelx_estimated_absorpt_T_min   0.658
_exptl_absorpt_coefficient_mu    0.951
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92542
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.82a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.379
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       rod
_exptl_crystal_F_000             1808
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0384
_diffrn_reflns_av_unetI/netI     0.0230
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            50310
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        66.880
_diffrn_reflns_theta_max         66.880
_diffrn_reflns_theta_min         3.070
_diffrn_ambient_temperature      173
_diffrn_detector                 'hybrid photon counting detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Dectris PILATUS P100K'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -23.00  47.00   1.00    1.00    --    0.00 -82.00  60.00   70
  2  ω    -20.00  35.00   1.00    1.00    --    0.00  77.00 -90.00   55
  3  ω    -20.00  35.00   1.00    1.00    --    0.00  77.00 -30.00   55
  4  ω    -83.00 -12.00   1.00    1.00    --    0.00 -19.00  60.00   71
  5  ω    -83.00 -12.00   1.00    1.00    --    0.00 -19.00   0.00   71
  6  ω    -15.00  35.00   1.00    1.00    --    5.00  77.00 120.00   50
  7  ω    -15.00  35.00   1.00    1.00    --    5.00  77.00  60.00   50
  8  ω    -15.00  35.00   1.00    1.00    --    5.00  77.00-150.00   50
  9  ω    -78.00  -7.00   1.00    1.00    --    5.00 -19.00 -60.00   71
 10  ω     17.00  94.00   1.00    1.00    --    5.00  19.00  60.00   77
 11  ω   -141.00 -25.00   1.00    1.00    --  -57.40 -57.00-120.00  116
 12  ω    -70.00  32.00   1.00    1.00    --  -57.40  57.00 -60.00  102
 13  ω   -141.00 -88.00   1.00    1.00    --  -57.40 -77.00  30.00   53
 14  ω   -141.00 -88.00   1.00    1.00    --  -57.40 -77.00  90.00   53
 15  ω   -141.00 -53.00   1.00    1.00    --  -57.40 -37.00 150.00   88
 16  ω   -141.00 -69.00   1.00    1.00    --  -57.40 -19.00  30.00   72
 17  ω   -141.00 -69.00   1.00    1.00    --  -57.40 -19.00-120.00   72
 18  ω   -141.00 -25.00   1.00    1.00    --  -57.40 -57.00-150.00  116
 19  ω   -101.00   6.00   1.00    1.00    --  -83.30  77.00 -60.00  107
 20  ω    -97.00 -20.00   1.00    1.00    -- -109.20  82.00 -57.77   77
 21  ω    -97.00 -20.00   1.00    1.00    -- -109.20  82.00  56.07   77
 22  ω   -124.00 -20.00   1.00    1.00    -- -109.20  63.00  11.81  104
 23  ω   -193.00-107.00   1.00    1.00    -- -109.20 -35.00  93.67   86
 24  ω   -193.00 -71.00   1.00    1.00    -- -109.20 -71.00-123.46  122
 25  ω   -112.00 -20.00   1.00    1.00    -- -109.20  37.00  90.00   92
 26  ω   -193.00 -71.00   1.00    1.00    -- -109.20 -70.00 155.55  122
 27  ω   -193.00 -76.00   1.00    1.00    -- -109.20 -60.00 167.74  117
 28  ω   -193.00 -72.00   1.00    1.00    -- -109.20 -69.00  71.26  121
 29  ω   -193.00 -96.00   1.00    1.00    -- -109.20 -45.00-153.60   97
 30  ω    -97.00 -20.00   1.00    1.00    -- -109.20  82.00-155.28   77
 31  ω   -193.00 -69.00   1.00    1.00    -- -109.20 -73.00-171.60  124
 32  ω   -193.00 -69.00   1.00    1.00    -- -109.20 -73.00-138.27  124
 33  ω   -193.00 -88.00   1.00    1.00    -- -109.20 -77.00  50.84  105
 34  ω    -87.00 -21.00   1.00    1.00    -- -109.20  82.00  30.13   66
 35  ω   -191.00-100.00   1.00    1.00    -- -109.20 -77.00 136.95   91
 36  ω   -124.00 -72.00   1.00    1.00    -- -109.20 -71.00 -98.64   52
 37  ω    -58.00 -30.00   1.00    1.00    -- -109.20  81.00-137.55   28
 38  ω   -154.00-128.00   1.00    1.00    -- -109.20 -71.00 -98.64   26
 39  ω   -125.00 -95.00   1.00    1.00    -- -109.20 -48.00  57.55   30
 40  ω   -120.00 -70.00   1.00    1.00    -- -109.20 -72.00-107.92   50
 41  ω   -155.00-115.00   1.00    1.00    -- -109.20 -27.00  67.72   40
 42  ω   -155.00-130.00   1.00    1.00    -- -109.20 -25.00 173.05   25
 43  ω    -99.00 -73.00   1.00    1.00    -- -109.20 -71.00-117.31   26
 44  ω   -187.00-135.00   1.00    1.00    -- -109.20 -35.00  19.24   52
 45  ω    -97.00 -44.00   1.00    1.00    -- -109.20  82.00 -15.94   53
 46  ω   -162.00-136.00   1.00    1.00    -- -109.20 -48.00  57.55   26
 47  ω   -176.00-146.00   1.00    1.00    -- -109.20 -33.00 105.01   30
 48  ω   -138.00-109.00   1.00    1.00    -- -109.20 -33.00 105.01   29
 49  ω   -160.00-132.00   1.00    1.00    -- -109.20 -71.00-117.31   28
 50  ω   -121.00 -86.00   1.00    1.00    -- -109.20 -52.00 -61.02   35
 51  ω   -117.00 -91.00   1.00    1.00    -- -109.20 -51.00  89.07   26
 52  ω   -132.00 -73.00   1.00    1.00    -- -109.20 -72.00-155.25   59
 53  ω    -97.00 -59.00   1.00    1.00    -- -109.20  82.00-110.87   38
 54  ω   -191.00-150.00   1.00    1.00    -- -109.20 -63.00 119.79   41
 55  ω   -175.00-149.00   1.00    1.00    -- -109.20 -51.00  89.07   26
 56  ω   -112.00 -68.00   1.00    1.00    -- -109.20  61.00 148.51   44
 57  ω   -102.00 -76.00   1.00    1.00    -- -109.20 -63.00 119.79   26
 58  ω   -102.00 -70.00   1.00    1.00    -- -109.20 -72.00-132.35   32
 59  ω   -161.00-136.00   1.00    1.00    -- -109.20 -19.00 -30.00   25
 60  ω    -73.00 -39.00   1.00    1.00    -- -109.20  82.00  18.83   34
 61  ω    -65.00 -39.00   1.00    1.00    -- -109.20  81.00 154.81   26
 62  ω    -92.00 -66.00   1.00    1.00    -- -109.20  77.00-120.00   26
 63  ω   -156.00-127.00   1.00    1.00    -- -109.20 -72.00-132.35   29
;
_diffrn_measurement_device       'AFC12: Kappa 4 circle'
_diffrn_measurement_device_type  'Rigaku XtaLAB P100K'
_diffrn_measurement_method       'shutterless scans'
_diffrn_measurement_specimen_support Loop
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0300720000
_diffrn_orient_matrix_UB_12      0.0423487000
_diffrn_orient_matrix_UB_13      0.0576382000
_diffrn_orient_matrix_UB_21      0.0516922000
_diffrn_orient_matrix_UB_22      0.0622185000
_diffrn_orient_matrix_UB_23      -0.0383874000
_diffrn_orient_matrix_UB_31      -0.1429628000
_diffrn_orient_matrix_UB_32      0.0314152000
_diffrn_orient_matrix_UB_33      -0.0017617000
_diffrn_radiation_monochromator  'Rigaku Osmic Confocal Optical System'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating Anode'
_diffrn_source_type              'Rigaku MM-007HF'
_reflns_Friedel_coverage         0.777
_reflns_Friedel_fraction_full    0.989
_reflns_Friedel_fraction_max     0.989
_reflns_number_gt                7225
_reflns_number_total             7389
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.82a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.82a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.82a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.116
_refine_diff_density_min         -0.174
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details 
;
 Flack x determined using 3107 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.02(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     569
_refine_ls_number_reflns         7389
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0263
_refine_ls_R_factor_gt           0.0257
_refine_ls_restrained_S_all      1.016
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0382P)²+0.5087P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0673
_refine_ls_wR_factor_ref         0.0677
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 N43-H43 = N13-H13
 0.98 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 C10(H10), C40(H40)
3.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C11(H11A,H11B), C14(H14A,H14B), C24(H24A,H24B), C39(H39A,H39B),
 C41(H41A,H41B), C44(H44A,H44B), C54(H54A,H54B)
3.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C16(H16), C17(H17), C18(H18), C19(H19),
 C20(H20), C34(H34), C35(H35), C36(H36), C37(H37), C46(H46), C47(H47), C48(H48),
  C49(H49), C50(H50)
3.d Idealised Me refined as rotating group:
 C25(H25A,H25B,H25C), C55(H55A,H55B,H55C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.37201(14) 0.21486(7) 0.84387(5) 0.0510(3) Uani 1 1 d . . . . .
F2 F 0.50660(17) 0.29111(8) 0.80734(6) 0.0685(4) Uani 1 1 d . . . . .
F3 F 0.55058(15) 0.18089(9) 0.79866(6) 0.0710(4) Uani 1 1 d . . . . .
O2 O 0.52702(16) 0.10611(7) 0.68286(7) 0.0474(4) Uani 1 1 d . . . . .
O12 O 0.10692(13) 0.18346(6) 0.76876(6) 0.0335(3) Uani 1 1 d . . . . .
O22 O 0.25627(17) 0.19194(9) 0.63037(7) 0.0532(4) Uani 1 1 d . . . . .
O23 O 0.42381(16) 0.23922(10) 0.57673(6) 0.0510(4) Uani 1 1 d . . . . .
N13 N 0.03994(16) 0.29557(8) 0.78766(7) 0.0325(3) Uani 1 1 d D . . . .
H13 H 0.060(2) 0.3428(10) 0.7823(10) 0.043(6) Uiso 1 1 d D . . . .
C1 C 0.45829(18) 0.23045(9) 0.68142(8) 0.0295(4) Uani 1 1 d . . . . .
C2 C 0.55929(19) 0.16759(9) 0.67670(8) 0.0329(4) Uani 1 1 d . . . . .
C3 C 0.69125(18) 0.19679(10) 0.66221(8) 0.0315(4) Uani 1 1 d . . . . .
C4 C 0.8093(2) 0.15998(11) 0.64963(9) 0.0381(4) Uani 1 1 d . . . . .
H4 H 0.810944 0.109678 0.650062 0.046 Uiso 1 1 calc R U . . .
C5 C 0.9238(2) 0.19822(12) 0.63652(9) 0.0427(5) Uani 1 1 d . . . . .
H5 H 1.005581 0.174375 0.627680 0.051 Uiso 1 1 calc R U . . .
C6 C 0.91909(19) 0.27180(12) 0.63628(8) 0.0401(4) Uani 1 1 d . . . . .
H6 H 0.998872 0.297581 0.627708 0.048 Uiso 1 1 calc R U . . .
C7 C 0.80199(19) 0.30857(11) 0.64812(8) 0.0354(4) Uani 1 1 d . . . . .
H7 H 0.800616 0.358862 0.647376 0.043 Uiso 1 1 calc R U . . .
C8 C 0.68613(18) 0.27028(10) 0.66116(7) 0.0305(4) Uani 1 1 d . . . . .
C9 C 0.54638(18) 0.29754(9) 0.67443(9) 0.0331(4) Uani 1 1 d . . . . .
H9A H 0.513231 0.327439 0.641009 0.040 Uiso 1 1 calc R U . . .
H9B H 0.545795 0.325827 0.711906 0.040 Uiso 1 1 calc R U . . .
C10 C 0.37131(17) 0.22475(9) 0.73871(8) 0.0280(3) Uani 1 1 d . . . . .
H10 H 0.328246 0.176917 0.737517 0.034 Uiso 1 1 calc R U . . .
C11 C 0.25621(18) 0.27860(9) 0.74153(8) 0.0306(4) Uani 1 1 d . . . . .
H11A H 0.284682 0.319419 0.766398 0.037 Uiso 1 1 calc R U . . .
H11B H 0.237620 0.296319 0.700471 0.037 Uiso 1 1 calc R U . . .
C12 C 0.12746(18) 0.24758(8) 0.76773(7) 0.0271(3) Uani 1 1 d . . . . .
C14 C -0.09195(19) 0.27779(10) 0.81188(9) 0.0364(4) Uani 1 1 d . . . . .
H14A H -0.107889 0.226403 0.806679 0.044 Uiso 1 1 calc R U . . .
H14B H -0.161777 0.303412 0.788777 0.044 Uiso 1 1 calc R U . . .
C15 C -0.10547(19) 0.29642(9) 0.87778(8) 0.0323(4) Uani 1 1 d . . . . .
C16 C -0.0043(2) 0.28118(10) 0.91833(9) 0.0398(4) Uani 1 1 d . . . . .
H16 H 0.076619 0.259799 0.904697 0.048 Uiso 1 1 calc R U . . .
C17 C -0.0202(2) 0.29696(12) 0.97903(10) 0.0479(5) Uani 1 1 d . . . . .
H17 H 0.049858 0.286186 1.006603 0.057 Uiso 1 1 calc R U . . .
C18 C -0.1368(2) 0.32810(12) 0.99935(10) 0.0480(5) Uani 1 1 d . . . . .
H18 H -0.147149 0.338953 1.040798 0.058 Uiso 1 1 calc R U . . .
C19 C -0.2383(2) 0.34343(12) 0.95947(10) 0.0471(5) Uani 1 1 d . . . . .
H19 H -0.319056 0.364764 0.973408 0.057 Uiso 1 1 calc R U . . .
C20 C -0.2231(2) 0.32775(11) 0.89864(10) 0.0399(4) Uani 1 1 d . . . . .
H20 H -0.293492 0.338534 0.871249 0.048 Uiso 1 1 calc R U . . .
C21 C 0.4512(2) 0.22767(11) 0.79641(9) 0.0400(4) Uani 1 1 d . . . . .
C22 C 0.3654(2) 0.21867(10) 0.62733(8) 0.0345(4) Uani 1 1 d . . . . .
C24 C 0.3461(3) 0.23221(15) 0.52102(9) 0.0565(6) Uani 1 1 d . . . . .
H24A H 0.289025 0.189336 0.523263 0.068 Uiso 1 1 calc R U . . .
H24B H 0.408396 0.226585 0.486619 0.068 Uiso 1 1 calc R U . . .
C25 C 0.2605(3) 0.29495(16) 0.51124(11) 0.0652(7) Uani 1 1 d . . . . .
H25A H 0.207262 0.288427 0.474571 0.098 Uiso 1 1 calc R U . . .
H25B H 0.317279 0.337070 0.507019 0.098 Uiso 1 1 calc R U . . .
H25C H 0.199989 0.301037 0.545647 0.098 Uiso 1 1 calc R U . . .
F31 F 0.29100(12) 0.43962(6) 0.70836(6) 0.0506(3) Uani 1 1 d . . . . .
F32 F 0.34062(12) 0.53369(7) 0.66048(7) 0.0516(3) Uani 1 1 d . . . . .
F33 F 0.27993(14) 0.44127(8) 0.61183(7) 0.0625(4) Uani 1 1 d . . . . .
O32 O 0.00296(15) 0.41964(7) 0.56157(6) 0.0418(3) Uani 1 1 d . . . . .
O42 O 0.01065(18) 0.44345(7) 0.77679(7) 0.0505(4) Uani 1 1 d . . . . .
O52 O -0.14099(16) 0.61083(8) 0.59481(7) 0.0456(3) Uani 1 1 d . . . . .
O53 O -0.16063(13) 0.51516(6) 0.65393(6) 0.0349(3) Uani 1 1 d . . . . .
N43 N -0.08761(16) 0.54753(8) 0.79973(7) 0.0312(3) Uani 1 1 d D . . . .
H43 H -0.097(2) 0.5928(10) 0.7885(9) 0.035(5) Uiso 1 1 d D . . . .
C31 C 0.05245(18) 0.53526(9) 0.60779(8) 0.0299(4) Uani 1 1 d . . . . .
C32 C 0.04267(18) 0.47989(9) 0.55538(8) 0.0319(4) Uani 1 1 d . . . . .
C33 C 0.08492(19) 0.51600(10) 0.50028(8) 0.0332(4) Uani 1 1 d . . . . .
C34 C 0.0838(2) 0.48995(11) 0.44166(9) 0.0402(4) Uani 1 1 d . . . . .
H34 H 0.053933 0.443185 0.433321 0.048 Uiso 1 1 calc R U . . .
C35 C 0.1272(2) 0.53382(13) 0.39615(9) 0.0488(5) Uani 1 1 d . . . . .
H35 H 0.126965 0.517549 0.355728 0.059 Uiso 1 1 calc R U . . .
C36 C 0.1713(3) 0.60206(13) 0.40943(10) 0.0524(6) Uani 1 1 d . . . . .
H36 H 0.201217 0.631710 0.377615 0.063 Uiso 1 1 calc R U . . .
C37 C 0.1728(2) 0.62781(11) 0.46752(10) 0.0426(5) Uani 1 1 d . . . . .
H37 H 0.202480 0.674647 0.475754 0.051 Uiso 1 1 calc R U . . .
C38 C 0.13006(18) 0.58365(10) 0.51362(8) 0.0333(4) Uani 1 1 d . . . . .
C39 C 0.1306(2) 0.59796(9) 0.58019(8) 0.0344(4) Uani 1 1 d . . . . .
H39A H 0.085524 0.643441 0.589312 0.041 Uiso 1 1 calc R U . . .
H39B H 0.223780 0.599643 0.595856 0.041 Uiso 1 1 calc R U . . .
C40 C 0.10816(18) 0.50083(9) 0.66597(8) 0.0294(4) Uani 1 1 d . . . . .
H40 H 0.056072 0.456079 0.671964 0.035 Uiso 1 1 calc R U . . .
C41 C 0.08610(19) 0.54571(9) 0.72309(8) 0.0313(4) Uani 1 1 d . . . . .
H41A H 0.174273 0.556655 0.741565 0.038 Uiso 1 1 calc R U . . .
H41B H 0.042812 0.591056 0.711941 0.038 Uiso 1 1 calc R U . . .
C42 C -0.0014(2) 0.50736(9) 0.76857(8) 0.0330(4) Uani 1 1 d . . . . .
C44 C -0.17872(19) 0.51749(10) 0.84471(9) 0.0353(4) Uani 1 1 d . . . . .
H44A H -0.191939 0.466616 0.835729 0.042 Uiso 1 1 calc R U . . .
H44B H -0.267260 0.541094 0.841093 0.042 Uiso 1 1 calc R U . . .
C45 C -0.13024(18) 0.52468(9) 0.90875(8) 0.0312(4) Uani 1 1 d . . . . .
C46 C -0.0007(2) 0.50599(12) 0.92466(9) 0.0439(5) Uani 1 1 d . . . . .
H46 H 0.060082 0.489534 0.894819 0.053 Uiso 1 1 calc R U . . .
C47 C 0.0410(2) 0.51115(14) 0.98398(10) 0.0541(6) Uani 1 1 d . . . . .
H47 H 0.130234 0.498292 0.994573 0.065 Uiso 1 1 calc R U . . .
C48 C -0.0464(2) 0.53483(13) 1.02764(10) 0.0511(5) Uani 1 1 d . . . . .
H48 H -0.017223 0.538836 1.068161 0.061 Uiso 1 1 calc R U . . .
C49 C -0.1754(2) 0.55254(13) 1.01241(10) 0.0482(5) Uani 1 1 d . . . . .
H49 H -0.236501 0.568066 1.042477 0.058 Uiso 1 1 calc R U . . .
C50 C -0.2166(2) 0.54779(11) 0.95313(9) 0.0397(4) Uani 1 1 d . . . . .
H50 H -0.306041 0.560689 0.942817 0.048 Uiso 1 1 calc R U . . .
C51 C 0.2536(2) 0.47949(10) 0.66130(9) 0.0383(4) Uani 1 1 d . . . . .
C52 C -0.0933(2) 0.55910(9) 0.61774(8) 0.0322(4) Uani 1 1 d . . . . .
C54 C -0.29428(19) 0.53965(10) 0.67137(10) 0.0400(4) Uani 1 1 d . . . . .
H54A H -0.348378 0.550633 0.635188 0.048 Uiso 1 1 calc R U . . .
H54B H -0.287145 0.583088 0.696094 0.048 Uiso 1 1 calc R U . . .
C55 C -0.3593(2) 0.48199(12) 0.70658(10) 0.0448(5) Uani 1 1 d . . . . .
H55A H -0.386644 0.443817 0.679351 0.067 Uiso 1 1 calc R U . . .
H55B H -0.438616 0.500717 0.727346 0.067 Uiso 1 1 calc R U . . .
H55C H -0.295400 0.463477 0.736226 0.067 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C21 1.339(2) . ?
F2 C21 1.341(2) . ?
F3 C21 1.326(3) . ?
O2 C2 1.212(2) . ?
O12 C12 1.228(2) . ?
O22 C22 1.199(3) . ?
O23 C22 1.325(2) . ?
O23 C24 1.466(3) . ?
N13 H13 0.922(18) . ?
N13 C12 1.332(2) . ?
N13 C14 1.457(2) . ?
C1 C2 1.558(2) . ?
C1 C9 1.548(2) . ?
C1 C10 1.544(2) . ?
C1 C22 1.533(3) . ?
C2 C3 1.459(3) . ?
C3 C4 1.393(3) . ?
C3 C8 1.389(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.379(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.390(3) . ?
C6 H6 0.9500 . ?
C6 C7 1.381(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.391(3) . ?
C8 C9 1.511(2) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10 1.0000 . ?
C10 C11 1.532(2) . ?
C10 C21 1.510(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.524(2) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C15 1.513(3) . ?
C15 C16 1.381(3) . ?
C15 C20 1.390(3) . ?
C16 H16 0.9500 . ?
C16 C17 1.392(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.377(3) . ?
C18 H18 0.9500 . ?
C18 C19 1.374(3) . ?
C19 H19 0.9500 . ?
C19 C20 1.393(3) . ?
C20 H20 0.9500 . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C24 C25 1.475(4) . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
F31 C51 1.342(2) . ?
F32 C51 1.340(2) . ?
F33 C51 1.342(2) . ?
O32 C32 1.212(2) . ?
O42 C42 1.226(2) . ?
O52 C52 1.200(2) . ?
O53 C52 1.336(2) . ?
O53 C54 1.459(2) . ?
N43 H43 0.896(18) . ?
N43 C42 1.338(2) . ?
N43 C44 1.464(2) . ?
C31 C32 1.569(2) . ?
C31 C39 1.544(2) . ?
C31 C40 1.550(2) . ?
C31 C52 1.534(3) . ?
C32 C33 1.464(3) . ?
C33 C34 1.393(3) . ?
C33 C38 1.386(3) . ?
C34 H34 0.9500 . ?
C34 C35 1.377(3) . ?
C35 H35 0.9500 . ?
C35 C36 1.393(4) . ?
C36 H36 0.9500 . ?
C36 C37 1.381(3) . ?
C37 H37 0.9500 . ?
C37 C38 1.388(3) . ?
C38 C39 1.505(3) . ?
C39 H39A 0.9900 . ?
C39 H39B 0.9900 . ?
C40 H40 1.0000 . ?
C40 C41 1.543(2) . ?
C40 C51 1.505(3) . ?
C41 H41A 0.9900 . ?
C41 H41B 0.9900 . ?
C41 C42 1.518(3) . ?
C44 H44A 0.9900 . ?
C44 H44B 0.9900 . ?
C44 C45 1.510(3) . ?
C45 C46 1.381(3) . ?
C45 C50 1.379(3) . ?
C46 H46 0.9500 . ?
C46 C47 1.386(3) . ?
C47 H47 0.9500 . ?
C47 C48 1.378(3) . ?
C48 H48 0.9500 . ?
C48 C49 1.367(3) . ?
C49 H49 0.9500 . ?
C49 C50 1.384(3) . ?
C50 H50 0.9500 . ?
C54 H54A 0.9900 . ?
C54 H54B 0.9900 . ?
C54 C55 1.489(3) . ?
C55 H55A 0.9800 . ?
C55 H55B 0.9800 . ?
C55 H55C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C22 O23 C24 117.43(17) . . ?
C12 N13 H13 118.2(15) . . ?
C12 N13 C14 123.66(15) . . ?
C14 N13 H13 117.8(14) . . ?
C9 C1 C2 104.60(14) . . ?
C10 C1 C2 111.31(14) . . ?
C10 C1 C9 117.18(14) . . ?
C22 C1 C2 103.00(14) . . ?
C22 C1 C9 112.39(15) . . ?
C22 C1 C10 107.47(14) . . ?
O2 C2 C1 123.46(17) . . ?
O2 C2 C3 128.67(18) . . ?
C3 C2 C1 107.84(15) . . ?
C4 C3 C2 127.85(17) . . ?
C8 C3 C2 110.39(16) . . ?
C8 C3 C4 121.75(18) . . ?
C3 C4 H4 120.8 . . ?
C5 C4 C3 118.47(19) . . ?
C5 C4 H4 120.8 . . ?
C4 C5 H5 120.1 . . ?
C4 C5 C6 119.75(19) . . ?
C6 C5 H5 120.1 . . ?
C5 C6 H6 119.0 . . ?
C7 C6 C5 122.02(19) . . ?
C7 C6 H6 119.0 . . ?
C6 C7 H7 120.8 . . ?
C6 C7 C8 118.48(18) . . ?
C8 C7 H7 120.8 . . ?
C3 C8 C7 119.51(17) . . ?
C3 C8 C9 111.76(15) . . ?
C7 C8 C9 128.72(17) . . ?
C1 C9 H9A 110.7 . . ?
C1 C9 H9B 110.7 . . ?
C8 C9 C1 105.14(14) . . ?
C8 C9 H9A 110.7 . . ?
C8 C9 H9B 110.7 . . ?
H9A C9 H9B 108.8 . . ?
C1 C10 H10 106.3 . . ?
C11 C10 C1 113.95(14) . . ?
C11 C10 H10 106.3 . . ?
C21 C10 C1 113.83(15) . . ?
C21 C10 H10 106.3 . . ?
C21 C10 C11 109.51(15) . . ?
C10 C11 H11A 109.0 . . ?
C10 C11 H11B 109.0 . . ?
H11A C11 H11B 107.8 . . ?
C12 C11 C10 112.83(14) . . ?
C12 C11 H11A 109.0 . . ?
C12 C11 H11B 109.0 . . ?
O12 C12 N13 123.77(17) . . ?
O12 C12 C11 121.73(16) . . ?
N13 C12 C11 114.48(14) . . ?
N13 C14 H14A 109.1 . . ?
N13 C14 H14B 109.1 . . ?
N13 C14 C15 112.61(16) . . ?
H14A C14 H14B 107.8 . . ?
C15 C14 H14A 109.1 . . ?
C15 C14 H14B 109.1 . . ?
C16 C15 C14 121.29(17) . . ?
C16 C15 C20 118.89(18) . . ?
C20 C15 C14 119.79(18) . . ?
C15 C16 H16 119.8 . . ?
C15 C16 C17 120.42(19) . . ?
C17 C16 H16 119.8 . . ?
C16 C17 H17 119.8 . . ?
C18 C17 C16 120.4(2) . . ?
C18 C17 H17 119.8 . . ?
C17 C18 H18 120.1 . . ?
C19 C18 C17 119.8(2) . . ?
C19 C18 H18 120.1 . . ?
C18 C19 H19 119.9 . . ?
C18 C19 C20 120.1(2) . . ?
C20 C19 H19 119.9 . . ?
C15 C20 C19 120.4(2) . . ?
C15 C20 H20 119.8 . . ?
C19 C20 H20 119.8 . . ?
F1 C21 F2 105.07(16) . . ?
F1 C21 C10 110.71(16) . . ?
F2 C21 C10 113.76(16) . . ?
F3 C21 F1 106.73(16) . . ?
F3 C21 F2 106.41(18) . . ?
F3 C21 C10 113.56(17) . . ?
O22 C22 O23 124.61(18) . . ?
O22 C22 C1 124.22(17) . . ?
O23 C22 C1 111.12(16) . . ?
O23 C24 H24A 109.5 . . ?
O23 C24 H24B 109.5 . . ?
O23 C24 C25 110.9(2) . . ?
H24A C24 H24B 108.1 . . ?
C25 C24 H24A 109.5 . . ?
C25 C24 H24B 109.5 . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C52 O53 C54 114.81(15) . . ?
C42 N43 H43 117.5(14) . . ?
C42 N43 C44 122.05(15) . . ?
C44 N43 H43 119.9(14) . . ?
C39 C31 C32 104.29(14) . . ?
C39 C31 C40 118.27(15) . . ?
C40 C31 C32 111.28(14) . . ?
C52 C31 C32 104.14(14) . . ?
C52 C31 C39 107.95(14) . . ?
C52 C31 C40 109.89(14) . . ?
O32 C32 C31 124.14(16) . . ?
O32 C32 C33 128.74(17) . . ?
C33 C32 C31 107.09(14) . . ?
C34 C33 C32 128.06(18) . . ?
C38 C33 C32 110.05(16) . . ?
C38 C33 C34 121.88(18) . . ?
C33 C34 H34 120.9 . . ?
C35 C34 C33 118.2(2) . . ?
C35 C34 H34 120.9 . . ?
C34 C35 H35 120.0 . . ?
C34 C35 C36 119.9(2) . . ?
C36 C35 H35 120.0 . . ?
C35 C36 H36 119.1 . . ?
C37 C36 C35 121.9(2) . . ?
C37 C36 H36 119.1 . . ?
C36 C37 H37 120.8 . . ?
C36 C37 C38 118.4(2) . . ?
C38 C37 H37 120.8 . . ?
C33 C38 C37 119.64(18) . . ?
C33 C38 C39 112.16(16) . . ?
C37 C38 C39 128.14(18) . . ?
C31 C39 H39A 110.8 . . ?
C31 C39 H39B 110.8 . . ?
C38 C39 C31 104.58(14) . . ?
C38 C39 H39A 110.8 . . ?
C38 C39 H39B 110.8 . . ?
H39A C39 H39B 108.9 . . ?
C31 C40 H40 106.3 . . ?
C41 C40 C31 113.97(14) . . ?
C41 C40 H40 106.3 . . ?
C51 C40 C31 113.45(15) . . ?
C51 C40 H40 106.3 . . ?
C51 C40 C41 109.90(16) . . ?
C40 C41 H41A 109.3 . . ?
C40 C41 H41B 109.3 . . ?
H41A C41 H41B 108.0 . . ?
C42 C41 C40 111.60(14) . . ?
C42 C41 H41A 109.3 . . ?
C42 C41 H41B 109.3 . . ?
O42 C42 N43 122.90(18) . . ?
O42 C42 C41 120.85(17) . . ?
N43 C42 C41 116.22(15) . . ?
N43 C44 H44A 108.7 . . ?
N43 C44 H44B 108.7 . . ?
N43 C44 C45 114.35(15) . . ?
H44A C44 H44B 107.6 . . ?
C45 C44 H44A 108.7 . . ?
C45 C44 H44B 108.7 . . ?
C46 C45 C44 121.08(17) . . ?
C50 C45 C44 120.32(17) . . ?
C50 C45 C46 118.55(18) . . ?
C45 C46 H46 119.9 . . ?
C45 C46 C47 120.29(19) . . ?
C47 C46 H46 119.9 . . ?
C46 C47 H47 119.8 . . ?
C48 C47 C46 120.3(2) . . ?
C48 C47 H47 119.8 . . ?
C47 C48 H48 120.1 . . ?
C49 C48 C47 119.7(2) . . ?
C49 C48 H48 120.1 . . ?
C48 C49 H49 120.1 . . ?
C48 C49 C50 119.9(2) . . ?
C50 C49 H49 120.1 . . ?
C45 C50 C49 121.19(19) . . ?
C45 C50 H50 119.4 . . ?
C49 C50 H50 119.4 . . ?
F31 C51 C40 111.26(16) . . ?
F32 C51 F31 105.09(16) . . ?
F32 C51 F33 105.89(16) . . ?
F32 C51 C40 114.63(15) . . ?
F33 C51 F31 106.49(16) . . ?
F33 C51 C40 112.83(17) . . ?
O52 C52 O53 124.34(18) . . ?
O52 C52 C31 123.44(18) . . ?
O53 C52 C31 112.21(15) . . ?
O53 C54 H54A 110.2 . . ?
O53 C54 H54B 110.2 . . ?
O53 C54 C55 107.66(16) . . ?
H54A C54 H54B 108.5 . . ?
C55 C54 H54A 110.2 . . ?
C55 C54 H54B 110.2 . . ?
C54 C55 H55A 109.5 . . ?
C54 C55 H55B 109.5 . . ?
C54 C55 H55C 109.5 . . ?
H55A C55 H55B 109.5 . . ?
H55A C55 H55C 109.5 . . ?
H55B C55 H55C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N13 H13 O42 0.922(18) 1.97(2) 2.8181(19) 153(2) . yes
N43 H43 O12 0.896(18) 2.136(18) 2.9911(19) 159.5(18) 3_556 yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 C2 C3 C4 3.0(3) . . . . ?
O2 C2 C3 C8 -178.11(19) . . . . ?
N13 C14 C15 C16 -44.2(2) . . . . ?
N13 C14 C15 C20 137.58(18) . . . . ?
C1 C2 C3 C4 -175.10(17) . . . . ?
C1 C2 C3 C8 3.8(2) . . . . ?
C1 C10 C11 C12 141.11(15) . . . . ?
C1 C10 C21 F1 -173.34(15) . . . . ?
C1 C10 C21 F2 68.6(2) . . . . ?
C1 C10 C21 F3 -53.3(2) . . . . ?
C2 C1 C9 C8 4.63(18) . . . . ?
C2 C1 C10 C11 -171.50(15) . . . . ?
C2 C1 C10 C21 61.94(19) . . . . ?
C2 C1 C22 O22 100.0(2) . . . . ?
C2 C1 C22 O23 -77.45(18) . . . . ?
C2 C3 C4 C5 179.53(18) . . . . ?
C2 C3 C8 C7 -179.95(16) . . . . ?
C2 C3 C8 C9 -0.7(2) . . . . ?
C3 C4 C5 C6 0.1(3) . . . . ?
C3 C8 C9 C1 -2.6(2) . . . . ?
C4 C3 C8 C7 -1.0(3) . . . . ?
C4 C3 C8 C9 178.25(17) . . . . ?
C4 C5 C6 C7 -0.8(3) . . . . ?
C5 C6 C7 C8 0.6(3) . . . . ?
C6 C7 C8 C3 0.3(3) . . . . ?
C6 C7 C8 C9 -178.79(18) . . . . ?
C7 C8 C9 C1 176.51(17) . . . . ?
C8 C3 C4 C5 0.8(3) . . . . ?
C9 C1 C2 O2 176.59(18) . . . . ?
C9 C1 C2 C3 -5.19(19) . . . . ?
C9 C1 C10 C11 68.2(2) . . . . ?
C9 C1 C10 C21 -58.4(2) . . . . ?
C9 C1 C22 O22 -147.98(19) . . . . ?
C9 C1 C22 O23 34.6(2) . . . . ?
C10 C1 C2 O2 49.1(2) . . . . ?
C10 C1 C2 C3 -132.66(15) . . . . ?
C10 C1 C9 C8 128.41(16) . . . . ?
C10 C1 C22 O22 -17.6(3) . . . . ?
C10 C1 C22 O23 164.92(15) . . . . ?
C10 C11 C12 O12 -20.7(2) . . . . ?
C10 C11 C12 N13 160.79(15) . . . . ?
C11 C10 C21 F1 57.8(2) . . . . ?
C11 C10 C21 F2 -60.2(2) . . . . ?
C11 C10 C21 F3 177.85(16) . . . . ?
C12 N13 C14 C15 115.05(19) . . . . ?
C14 N13 C12 O12 -1.4(3) . . . . ?
C14 N13 C12 C11 177.09(16) . . . . ?
C14 C15 C16 C17 -178.21(18) . . . . ?
C14 C15 C20 C19 178.26(19) . . . . ?
C15 C16 C17 C18 -0.1(3) . . . . ?
C16 C15 C20 C19 0.0(3) . . . . ?
C16 C17 C18 C19 0.2(3) . . . . ?
C17 C18 C19 C20 -0.2(3) . . . . ?
C18 C19 C20 C15 0.1(3) . . . . ?
C20 C15 C16 C17 0.0(3) . . . . ?
C21 C10 C11 C12 -90.10(18) . . . . ?
C22 O23 C24 C25 86.1(3) . . . . ?
C22 C1 C2 O2 -65.8(2) . . . . ?
C22 C1 C2 C3 112.46(16) . . . . ?
C22 C1 C9 C8 -106.39(16) . . . . ?
C22 C1 C10 C11 -59.42(18) . . . . ?
C22 C1 C10 C21 174.01(15) . . . . ?
C24 O23 C22 O22 3.5(3) . . . . ?
C24 O23 C22 C1 -179.07(17) . . . . ?
O32 C32 C33 C34 2.9(3) . . . . ?
O32 C32 C33 C38 -176.8(2) . . . . ?
N43 C44 C45 C46 -48.6(2) . . . . ?
N43 C44 C45 C50 133.73(18) . . . . ?
C31 C32 C33 C34 -175.00(19) . . . . ?
C31 C32 C33 C38 5.3(2) . . . . ?
C31 C40 C41 C42 118.23(17) . . . . ?
C31 C40 C51 F31 -169.61(15) . . . . ?
C31 C40 C51 F32 71.3(2) . . . . ?
C31 C40 C51 F33 -50.0(2) . . . . ?
C32 C31 C39 C38 13.25(19) . . . . ?
C32 C31 C40 C41 -164.79(14) . . . . ?
C32 C31 C40 C51 68.41(19) . . . . ?
C32 C31 C52 O52 -94.8(2) . . . . ?
C32 C31 C52 O53 84.28(17) . . . . ?
C32 C33 C34 C35 179.3(2) . . . . ?
C32 C33 C38 C37 -178.83(18) . . . . ?
C32 C33 C38 C39 3.7(2) . . . . ?
C33 C34 C35 C36 0.4(3) . . . . ?
C33 C38 C39 C31 -11.1(2) . . . . ?
C34 C33 C38 C37 1.5(3) . . . . ?
C34 C33 C38 C39 -176.05(18) . . . . ?
C34 C35 C36 C37 -0.2(4) . . . . ?
C35 C36 C37 C38 0.6(3) . . . . ?
C36 C37 C38 C33 -1.2(3) . . . . ?
C36 C37 C38 C39 175.9(2) . . . . ?
C37 C38 C39 C31 171.69(19) . . . . ?
C38 C33 C34 C35 -1.0(3) . . . . ?
C39 C31 C32 O32 170.30(18) . . . . ?
C39 C31 C32 C33 -11.67(19) . . . . ?
C39 C31 C40 C41 74.5(2) . . . . ?
C39 C31 C40 C51 -52.3(2) . . . . ?
C39 C31 C52 O52 15.6(2) . . . . ?
C39 C31 C52 O53 -165.29(14) . . . . ?
C40 C31 C32 O32 41.7(2) . . . . ?
C40 C31 C32 C33 -140.25(16) . . . . ?
C40 C31 C39 C38 137.45(16) . . . . ?
C40 C31 C52 O52 145.93(18) . . . . ?
C40 C31 C52 O53 -35.00(19) . . . . ?
C40 C41 C42 O42 39.0(3) . . . . ?
C40 C41 C42 N43 -143.01(16) . . . . ?
C41 C40 C51 F31 61.49(19) . . . . ?
C41 C40 C51 F32 -57.6(2) . . . . ?
C41 C40 C51 F33 -178.89(15) . . . . ?
C42 N43 C44 C45 98.7(2) . . . . ?
C44 N43 C42 O42 -2.5(3) . . . . ?
C44 N43 C42 C41 179.54(16) . . . . ?
C44 C45 C46 C47 -178.3(2) . . . . ?
C44 C45 C50 C49 177.9(2) . . . . ?
C45 C46 C47 C48 0.1(4) . . . . ?
C46 C45 C50 C49 0.2(3) . . . . ?
C46 C47 C48 C49 0.8(4) . . . . ?
C47 C48 C49 C50 -1.2(4) . . . . ?
C48 C49 C50 C45 0.7(4) . . . . ?
C50 C45 C46 C47 -0.6(3) . . . . ?
C51 C40 C41 C42 -113.14(17) . . . . ?
C52 O53 C54 C55 174.86(16) . . . . ?
C52 C31 C32 O32 -76.6(2) . . . . ?
C52 C31 C32 C33 101.42(16) . . . . ?
C52 C31 C39 C38 -97.08(16) . . . . ?
C52 C31 C40 C41 -49.98(19) . . . . ?
C52 C31 C40 C51 -176.77(15) . . . . ?
C54 O53 C52 O52 -8.5(3) . . . . ?
C54 O53 C52 C31 172.48(14) . . . . ?

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: chloroform'
